Congrats on planning for your first Chanel bag! Very exciting! When I was planning for my first Chanel, I knew I wanted the medium Classic Flap and possibly a WOC. I was fortunate enough to get both of them together as my first Chanels and have since added a variety of styles, sizes and colors to my collection, including minis. Of the options you are considering, I would hands down recommend the medium CF as your first (especially if it may be your only) Chanel. I love my WOC and minis and use them a lot, but they aren't as versatile as my medium classic flaps. Though I don't have a small classic flap, it seems the medium is very heavily favored over the small size due to the negligible cost difference and the fact that the medium holds more. Besides, if you want to add a WOC or mini later, a medium classic flap will add more variety to your collection! Hopefully you can spend some time trying on a variety of styles and sizes so you can get a real feel of what speaks to you and works for you. Who knows...you may even fall for a Reissue or another style once you have a chance to try them on. GL!